2-Decarboxy-2-hydroxymethyl-3,7-inter-m-phenylene-ω-phenoxy-PGA11 compounds

ABSTRACT

This invention comprises certain analogs of the prostaglandins in which the C-1 carboxyl is replaced by a primary alcohol. Also provided in this invention, are novel chemical processes useful in the preparation of the above prostaglandin analogs. These prostaglandin analogs exhibit prostaglandin-like activity, and are accordingly useful for the same pharmacological purposes as the prostaglandins. Among these purposes are blood pressure lowering, labor induction at term, reproductive-cycle regulation, gastric antisecretory action, and the like.

The present application is a divisional application of Ser. No. 647,357, filed Jan. 8, 1976, now issued as U.S. Pat. No. 4,055,602.

The present invention relates to prostaglandin analogs, for which the essential material constituting disclosure therefor is incorporated by reference here from U.S. Pat. No. 4,055,602, issued Oct. 25, 1977. 

I claim:
 1. A prostaglandin analog of the formula ##STR1## WHEREIN Z₃ is oxa or methylene; WHEREIN D is ##STR2## wherein Y is trans-CH═CH-; wherein M₁ is ##STR3## wherein R₅ is hydrogen or methyl; WHEREIN L₁ is ##STR4## or a mixture of ##STR5## wherein R₃ and R₄ are hydrogen or methyl, being the same or different;Wherein g is 1, 2, or 3; and Wherein s is 0, 1, 2, or 3 and T is chloro, fluoro, trifluoromethyl, alkyl of one to 3 carbon atoms, inclusive, or alkoxy of 1 to 3 carbon atoms, inclusive, the various T's being the same or different, with the proviso that not more than two T's are other than alkyl.
 2. A compound according to claim 1, wherein D is ##STR6##
 3. A compound according to claim 2, wherein s is 0 or 1 and T is chloro, fluoro, or trifluoromethyl.
 4. A compound according to claim 3, wherein g is
 1. 5. A compound according to claim 4, wherein at least one of R₃ and R₄ is methyl.
 6. A compound according to claim 5, wherein R₃ and R₄ are both methyl.
 7. A compound according to claim 6, wherein R₅ is methyl.
 8. 2-Decarboxy-2-hydroxymethyl-5-15,16-dimethyl-16-phenoxy-3,7-inter-m-phenylene-3-oxa-4,5,6,18,19,20-hexanor-PGA₁, a compound according to claim
 7. 9. A compound according to claim 6, wherein R₅ is hydrogen.
 10. 2-Decarboxy-2-hydroxymethyl-16-methyl-16-phenoxy-3,7-inter-m-phenylene-3-oxa-4,5,6,18,19,20-hexanor-PGA₁, a compound according to claim
 9. 11. A compound according to claim 4, wherein R₃ and R₄ are both hydrogen.
 12. A compound according to claim 11, wherein R₅ is methyl.
 13. 2-Decarboxy-2-hydroxymethyl-15-methyl-16-phenoxy-3,7-inter-m-phenylene-3-oxa-4,5,6,17,18,19,20-heptanor-PGA₁, a compound according to claim
 12. 14. A compound according to claim 11, wherein R₅ is hydrogen.
 15. 2-Decarboxy-2-hydroxymethyl-16-phenoxy-3,7-inter-m-phenylene-3-oxa-4,5,6,17,18,19,20-heptanor-PGA₁, a compound according to claim
 14. 16. A compound according to claim 1, wherein D is ##STR7##
 17. A compound according to claim 16, wherein s is 0 or 1 and T is chloro, fluoro, or trifluoromethyl.
 18. A compound according to claim 17, wherein g is
 1. 19. A compound according to claim 18, wherein at least one of R₃ and R₄ is methyl.
 20. A compound according to claim 19, wherein R₃ and R₄ are both methyl.
 21. A compound according to claim 20, wherein R₅ is methyl.
 22. 2-Decarboxy-2-hydroxymethyl-15,16-dimethyl-16-phenoxy-3,7-inter-m-phenylene-3-oxa-4,5,6,18,19,20-hexanor-9-deoxy-9,10-didehydro-PGD, a compound according to claim
 21. 23. A compound according to claim 20, wherein R₅ is hydrogen.
 24. 2-Decarboxy-2-hydroxymethyl-16-methyl-16-phenoxy-3,7-inter-m-phenylene-3-oxa-4,5,6,18,19,20-hexanor-9-deoxy-9,10-didehydro-PGD₁, a compound according to claim
 23. 25. A compound according to claim 18, wherein R₃ and R₄ are both hydrogen.
 26. A compound according to claim 25, wherein R₅ is methyl.
 27. 2-Decarboxy-2-hydroxymethyl-15-methyl-16-phenoxy-3,7-inter-m-phenylene-3-oxa-4,5,6,17,18,19,20-heptanor-9-deoxy-9,10-didehydro-PGD.sub.1, a compound according to claim
 26. 28. A compound according to claim 25, wherein R₅ is hydrogen.
 29. 2-Decarboxy-2-hydroxymethyl-16-phenoxy-3,7-inter-m-phenylene-3-oxa-4,5,6,17,18,19,20-heptanor-9-deoxy-9,10-didehydro-PGD₁, a compound according to claim
 28. 